If you grew up in Chicago during the mid-2000s, you didn't just hear about Derrick Rose. You felt him. Long before he was the youngest MVP in NBA history or the guy whose knees broke a million hearts, he was just "Pooh" from Englewood. But even then, he wasn't "just" anything. The Derrick Rose high school era at Simeon Career Academy is the stuff of actual legend, not the manufactured kind we see on Instagram today. It was gritty. It was loud. It was arguably the most dominant run by a point guard in the history of Illinois basketball.
He wore number 25. That wasn't an accident. He wore it to honor Ben "Benji" Wilson, the Simeon star murdered in 1984 who was supposed to be the next Magic Johnson. Carrying that number in that gym? That’s pressure most 15-year-olds would collapse under. Rose didn't. He thrived.
The Simeon Culture and the Robert Smith Factor
You can't talk about Rose at Simeon without talking about Robert Smith. Coach Smith wasn't interested in feeding a teenager's ego. In fact, he famously sat Rose on the bench for stretches during his freshman year, making him earn every second of floor time. It sounds crazy now, right? Benching a future Hall of Famer. But it worked. It kept Rose humble, even as the hype train started moving faster than his crossover.
Simeon wasn't some private prep school recruiting from three states away. It was a public vocational school on the South Side. The Wolverines played a brand of basketball that was suffocating. If you walked into that gym on 81st and Vincennes, you weren't seeing "showcase" basketball. You were seeing a defensive clinic. Rose was the engine. Honestly, his passing back then was just as scary as his dunks. He had this weirdly telepathic connection with guys like Tim Flowers and Kevin Johnson. He would throw these cross-court bullets that looked like they were going out of bounds, only to land perfectly in a teammate's pocket for a layup.
Most people forget that Rose wasn't even the leading scorer all the time. He didn't need to be. He was obsessed with winning, a trait that arguably peaked during his junior and senior years when Simeon went back-to-back as state champions.
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That Legendary Senior Season (2006-2007)
By 2007, the Derrick Rose high school experience had turned into a traveling circus. People were showing up hours early just to get a seat in tiny high school gyms. Simeon went 33-2 that year. They weren't just beating teams; they were demoralizing them.
The schedule was brutal. They flew to California, New York, and everywhere in between. One of the most famous games from that run was against Oak Hill Academy, which was basically a pro team in high school jerseys. Brandon Jennings was there. Nolan Smith was there. It was televised on ESPN, back when that was a massive deal for high schoolers. Rose didn't just play; he controlled the game without forcing shots. That was the magic of his game. He had this "switch." He’d spend three quarters getting everyone else involved, and then in the fourth, he’d decide it was over. He’d rip a rebound, go coast-to-coast, and finish with a double-clutch layup that left the defenders looking at the rafters.
Breaking Down the Numbers (The Real Ones)
- Junior Year: Rose averaged about 20 points, 5.4 rebounds, and 8.7 assists.
- Senior Year: 25.2 points, 9.1 rebounds, and 8.8 assists.
- The Honors: Illinois Mr. Basketball, McDonald's All-American, and a Parade All-American.
He finished his high school career with a 120-12 record. Think about that for a second. In four years of high school basketball, playing against the best talent in the country, he only lost twelve times. That is a level of consistency that most NBA teams would kill for.
The Myth of the "Chicago Point Guard"
There is a specific DNA to Chicago guards. It’s a mix of toughness, handle, and an absolute refusal to back down. Rose is the blueprint for the modern version of that. Before him, you had Isiah Thomas and Tim Hardaway. After him? Well, everyone is still trying to catch up.
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When you watch old grainy footage of Rose at Simeon, the first thing you notice isn't the speed. It’s the balance. He could stop on a dime, pivot, and explode in a different direction while the defender was still sliding toward the baseline. It was physics-defying. He made elite high school defenders look like they were playing in work boots.
But it wasn't all highlights. There was real grit. Chicago basketball in the mid-2000s was physical. You got fouled hard. There were no "soft" whistles in the Public League. Rose took those hits and just kept coming. It prepared him for the NBA in a way that the modern "three-point-centric" high school game just doesn't.
The Recruitment Drama That Wasn't
Every big-time program wanted him. Coach K at Duke, Roy Williams at North Carolina, Bill Self at Kansas. They all made the trip to Chicago. But Rose was always a bit of an introvert. He didn't want the Hollywood lifestyle. He ended up choosing Memphis to play for John Calipari, mostly because of the relationship he built with the staff and the chance to play in a system that mirrored his speed.
Looking back, the Derrick Rose high school years were the last time we saw him play with a certain kind of reckless joy. Before the ACL tears, before the trade rumors, before the weight of being the "hometown savior" for the Bulls settled on his shoulders. At Simeon, he was just a kid who loved to pass the ball and happen to be able to jump over a parked car.
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Why We Still Talk About Those Simeon Days
Basketball fans are obsessed with "What Ifs." What if Rose never got hurt? What if he stayed in Chicago his whole career? But for a lot of us, the Simeon years are the purest part of his story. It was the rise. It was the gold jerseys and the blue trim. It was the "See Red" era before it even had a name.
If you want to understand why Chicago loves Derrick Rose so much—why they still cheer for him no matter what jersey he’s wearing—you have to look at those four years. He represented the city’s potential. He was the kid from a tough neighborhood who did everything right, stayed out of trouble, and became the best in the world.
What You Can Learn From the Rose Era
If you're a young player or a coach looking at Rose’s high school trajectory, there are a few real-world takeaways that actually matter:
- Patience is a weapon: Rose didn't complain when Coach Smith sat him as a freshman. He learned the system.
- The "Whole" Game matters: Rose was a 6'3" guard who averaged nearly 10 rebounds a game as a senior. He didn't just hang out on the perimeter.
- Defense wins championships: Those Simeon teams were built on stops. Rose’s ability to pressure the ball full-court changed games more than his scoring did.
- Loyalty counts: He stayed at his local school. He didn't jump to a national powerhouse for his senior year. He won with the guys he grew up with.
The Derrick Rose high school legacy isn't just about the trophies in the case at Simeon. It’s about the way he played the game. He played it like he had something to prove every single night, even when everyone already knew he was the best player on the floor.
Actionable Next Steps for Fans and Students of the Game
To truly appreciate what Rose did, you need to go beyond the stat sheet. Here is how to actually study the "Rose Era":
- Watch the "Full" Game Tapes: Don't just watch the 30-second mixtapes on YouTube. Look for full game replays of the 2007 Illinois State Championship or the Oak Hill vs. Simeon matchup. Watch his movement off the ball.
- Research the Benji Wilson Story: To understand why Rose wore 25, you have to understand Benji. Watching the documentary "Benji" (30 for 30) provides the necessary context for the weight Rose carried at Simeon.
- Study the "Dribble-Drive" Motion: If you're a player, look at how Rose used screens at the top of the key during his senior year. This was the precursor to the offense he would later run at Memphis.
- Visit the Chicago Public League Archives: Many of the best stories from Rose’s time aren't in national papers but in the archives of local Chicago publications like the Chicago Sun-Times or the Chicago Defender.
Derrick Rose didn't just play for Simeon; he defined an era of Chicago basketball that we might never see again. It was a perfect storm of talent, coaching, and timing. Even now, twenty years later, the echoes of those games still ring through the gyms of the South Side. If you're looking for the blueprint of a superstar, look no further than the kid in the number 25 jersey at 81st and Vincennes.